How do you follow up with prospects who initiated a conversation, but didn’t come back to you lately? Do you send a "just checking in" email or bubble your message to the top of their inbox?

Some of the worst follow-ups that you've either seen, you've received, or even sent (no judgment here, okay? I did the same):

  • Did you see my last email/voicemail?
  • Noticed you didn't reply to my email…
  • Just bumping this to the top of your inbox…
  • Just bubbling this to the top…
  • Just checking in to see if…
  • Just following up here…
  • Just poking my head back in…
  • Any update on this…
  • Any thoughts…
  • Happy Monday…
  • Hoping you had a good Easter Holidays…
  • Hope your family is doing well in these challenging times…

LinkedIn did a study on the most damaging word in follow-up emails and it's the word “just”.

Because it sounds like:

Oh, I just wanna do this, just wanna do that, just passing by, just trying to sell you stuff.

You see the pattern right? They make you come across as just another seller, and here I want to demonize the normal sales behavior a bit.

Typically, what are the characteristics that salespeople are known for and the things that they're known for doing?

  • pushy.
  • annoyingly persistent.
  • speak a lot
  • hard sell
  • overbearing
  • relentless
  • coin-operated
  • seller focused.
  • selling unnecessary stuff
  • single-minded agenda
  • not trustworthy
  • inauthentic
  • self-serving
  • intrusive
  • not customer oriented
  • slimy
  • irrelevant
  • impersonal
  • too persistent
  • overbearing

That is a lot of adjectives, I know, but they're all within the line of a salesperson image that your clients automatically see you as.

So within the structure of thinking like a salesperson, there is a normal pattern to how salespeople are reaching out.

Hence, the most toxic thing to your sales process is your buyer seeing you as a seller. If they see you as a seller, they're gonna associate all of this with you and this, in turn, is gonna make it really, really hard on you to sell.

Why? Well:

  • They're not gonna tell you their pain,
  • They're not gonna tell you their problem.
  • They're gonna choke back all of that in discovery because they don't trust you.
  • They're not gonna tell you if they have money.
  • They're not gonna tell you how much money they have.
  • They're not gonna tell you what the extra steps are in the process.
  • They're not gonna tell you what's going on in the middle of the deal.
  • They don't trust you.

So the most dangerous thing to you is someone looking at your email or someone hearing your cold call and thinking  “Oh, this is a salesperson”.

But what if there was a way to keep your prospects warm without resorting to typical sales tactics? Can you flip this on its head and focus on building genuine connections with your prospects?

In this article, we'll unpack nine different ways to prove to your prospects that you're not there to sell unnecessary stuff - you're there to help them.

9 followups that will charm your prospect

The printable & high-resolution version of this is available to download below.

By pattern interrupting and engaging your prospects in a more authentic way, you can effectively communicate your message from front to end of the selling process.

So, let's dive in and learn how to keep those deals warm without crossing the line into annoying territory.

Send over relevant content

Flip your mindset from:

“I need to follow up with this person, and I need to be aggressive about it.”


“I need to be aggressive about finding and adding value to my buyer.”

Imagine shifting from a routine to-do of following up with a person and asking about a proposal, to a more thoughtful approach of finding a valuable piece of content to share with them. Not only does this show that you're not only interested in just closing deals, but it also gives you a way to tactfully reach out. Even though the person might know what you're up to, the charm lies in how you do it.

This strategy has been a game-changer for me in closing deals. Rather than straight-up asking for an update, I comb the internet for something useful to send them. It's a way of continuously adding value to my prospect along the way, which increases the chances of renewal, upselling, cross-selling, closing deals, and scheduling meetings.

To step up your game, focus on sending over relevant third-party content. It provides a wider range of perspectives and builds credibility, so give it a shot. Remember, every time you send something, there's first, second, and third-party content to choose from.

Here, let’s stop for a second and explore the value of first, second and third-party content:

  • First-party content is data that you collect and analyze yourself.

Now, this can be a bit of a tricky subject, especially when it comes to prospecting. There's always a slight chance that people might doubt whether the information you're sharing is unbiased or not.

After all, you're selecting which bits of data to present and which ones to exclude. It's like being both the judge and the jury - and that's where the trust factor comes into play.

  • The second party is essentially your evaluation of someone else's data.

So basically someone else's first-party data. It’s honesty neither here nor there in terms of credibility and trust.

  • And third-party is basically, I want you to think like a review site.

Let me show you a neat tactic that works wonders - the power of third-party content:

STEP 1. Find an article or piece that was written by someone else in your industry, and send it over to your prospect.

By doing this, you're sending them something from an impartial source, and it shows you're not trying to push your own agenda onto them.

Preferably, something that doesn’t tie directly to your company, product, or even value proposition.

STEP 2. Make sure to highlight one specific point that really resonated with you and make it digestible for them.

When looking for articles, go for click-bait-style headlines, even if they sound cheesy. The key is to find something that strikes a chord and is easy to read.

For instance, instead of sharing bland articles on weight loss, go for the ones that promise you'll lose 20 pounds in a week by eating just three foods. It's the kind of thing that people want to read.

STEP 3. Now, when you send out the email with the third-party content, make sure you add that you're not expecting a response - this removes any unnecessary pressure.

So, I would look through for my buyer persona, what are the articles, that would really hit home for them. And I would just send them an email something like:


Saw this article the other day and thought of you.

And I especially liked point number…, where they said….

You're gonna think it sounds crazy, but no need to respond just thought you might wanna take a look.



Still, they might just reply with an update on the buying decision within their company or let you in on what's happening with their business. It's a great way to build rapport and cultivate trust without the overt sales pitch.

Send over an idea that will make things better for them

Here's an idea that will instantly elevate your selling game - try sending over an idea to your prospect that would make their lives better. It's not always about pitching your product or solution but providing value to their business in any way you can.

Let’s say you’re selling a call transcription tool to the VP of Sales in a SaaS company.

Think about it - your prospects have a hundred different things on their minds, and chances are they're running into various roadblocks on the way:

  • Are their reps sending out enough emails?
  • Are their reps held accountable?
  • Are they sending out quality emails?
  • What's the lead routing look like?
  • Are they sending it to the right accounts?
  • Are these the right people?
  • How's our collaboration with marketing?
  • How's the inbound team doing?

This list of problems is endless.

But if you can send them an idea that's easy to implement, doesn't require time or investment, and doesn't involve anyone internally, you're golden. And you’ll win a lot of rapport with them.

Surprise them with a killer idea that makes their world better without having any strings attached - it's a surefire way to win their hearts.

Your follow-up can look like this:


I heard this idea the other day and thought you might get some use out of it.


I know that you're using … for outreach. If you want to do X, Y, and Z, you can go to your settings and…



Pro tip: The more unrelated the idea is to your product, the better. They're probably expecting a sales pitch from you, so it's a pleasant surprise when you show up to help regardless of what's in it for you.

Knowing what's going on in the world

Staying up to date with the latest news and events is crucial in establishing genuine connections. It's all about being mindful of your prospect's time and attention. After all, it's their most valuable asset.

Take note of any recent developments in their world - whether it's a company acquisition or a shift in their role. Use this information as a starting point for reaching out to them. While this may seem outside of the sales realm, it's all about building a relationship that's not based solely on business.

Sending over an email that shows you understand their world can go a long way in earning their trust. Of course, this approach is harder to control, as it relies on external factors that are out of your reach. But when done well, it can lead to invaluable connections that stand the test of time.

So the first three points in this article are the ways that work least effectively. Now, we moving on to a real deal starting from the next point…

Assist with a pain point

Learning about your prospect's true pain points is key to building a successful relationship. As a salesperson, you either learn about these in the discovery phase or through conversations with your prospect.

But, here's the thing - if you can provide them with an easy solution to a problem they didn't even know they had, you'll instantly become a valuable asset. And the best part? This solution doesn't always have to be about your product - in fact, it's better if it isn't.

Showing prospects that you genuinely care about making their lives easier is a powerful way to earn their trust. Take a little time to find out what kinds of pain points your buyer persona typically experiences and then send over a solution tailored to their specific needs. It might take a little more time than the usual follow-up emails, but the payoff is much greater.

Remember to wrap up your email with a statement like, "No need to respond, just thought you might find value in this." It's a subtle way to let them know you value their time and that you're not just in it for sale.

Direct mail

If you're considering sending a direct mail package to a prospective customer, it's important to make it as personalized as possible. Think outside of the box and consider what they may enjoy or what's relevant to them.

For example, receiving a bottle of wine as a gift does nothing for your prospect if they’re a non-drinker. When you're personalizing your package, think about what would be meaningful and relevant to them.

But let’s say your prospect (VP of sales, for example) is a wine connoisseur. So you can send her an aerator with a message tailored to her passion. Something like “Letting wine breathe, enhances the flavor. Enabling sales reps to air out their sales conversations could help highlight their best practices.”

The lesson here is clear: when sending a direct mail package, don't just send something generic like cupcakes. Think carefully and creatively about what would be meaningful and relevant to the recipient. By personalizing your package, you're more likely to capture their attention and forge a lasting connection.

Make them aware of potential threats that they didn't know about

One of the biggest keys to closing deals quickly is identifying and solving your prospect's long-term problems. And while it may take a lot of effort, the payoff is well worth it.

So, instead of sending this boring just-checking-in kind of email you could send a personalized message with relevant stats, like “Do more than 30% of your demo requests don't lead to an actual demo? If yes, let me know and I’ll send over a process to alleviate that problem. OR Give me a call and I’ll share some solutions we use for the same”

The important thing is to find something that's not directly related to selling your product. Your goal should be to make yourself a trusted advisor and valuable resource to your customers.

This could be anything from an industry regulation change to a new competitive threat.

The reason? When you show your prospect that you genuinely care about helping them and their business, they'll be much more likely to trust you. This builds rapport and sets the foundation for a successful business relationship.

Sending a personalized email with data or insights that could be hurting their business is a powerful way to earn their trust. Remember, executive leaders spend all day searching for people who can tell them things they don't know about their business - this could be your chance to be that person for them.

And don't fall into the trap of just being nice or empathetic. Your real goal should be to earn credibility and rapport by finding and solving your prospect's problems.

If you can't name your top four buyer personas according to data who have closed the most often with you in terms of the level of title and discipline of title, and then can't name four metrics that they care about (not related to your product), then you don't know your buyer.

The problem is, that as founders or salespeople, we usually have all product information but not enough information (or even one sheet) on such kinds of details on our buyer persona.

So take the time to get to know your buyer personas: their terms, metrics, and even their typical jokes. The more you know about them, the better equipped you'll be to have meaningful conversations and solve their problems.

In short, invest in understanding your buyer, find problems that they're facing, and then offer solutions. When your prospect sees that you're dedicated to helping them succeed, they'll be much more likely to buy from you and trust your guidance.

Network connections

Play a matchmaker. And what I mean by that is you need to connect them to people, who might potentially be useful to them. So here you need to:

  • Introduce them/give a contact of people, who have a common connection in their role, who might be interesting for your prospect.
  • Focus on someone upmarket for them.
  • Connect them to someone who is passionate about the same topic or working on a similar project.

Those connections might come from your customers, colleagues from different departments, your own friend, or a friend of a friend.

The key here is to play a matchmaker and provide your prospect with something, that they didn’t ask for but won’t be able to refuse. And at the end of the day, new connections are always important and very much appreciated.


Bring them leads, it’s the best way to conquer your prospect’s heart. Here I advise to:

  • Refer leads to your prospects if you hear about anyone on the market.

Understand what they need and then provide it. It could be a great candidate for their departments, a new channel for lead generation, or sales leads themselves. The possibilities here are endless.


What does your prospect’s company follow? What communities are they in? Which events do they go to?

Analyze their social media activities, stalk them a bit, and find a way to bring even more value by inviting them to some of the communities where their buyer persona is.

This way you’ll cover a few very important processes:

  • You’ll learn more about your prospect.
  • You’ll learn more about their buyers.
  • You’ll bring more value and prove that you’re a very well-rounded sales rep, who wants to help, not to sell.

So, are you ready to take your sales game to the next level?

Then start thinking of value like a bank account: the more you deposit, the more you can withdraw later.

But what does that look like in practice? Well, I've introduced you to the nine ideas to get you started. These are tried-and-true ways to add value to your prospects and customers alike.

Now, here's the thing: these tactics aren't just for anyone. Use them strategically, when you've hit a roadblock in a deal or you're trying to get a foot in the door with a new prospect. By sharing these ideas without asking for anything in return, you're showing that you're genuinely interested in their success.

Is it hard to ask for nothing? Absolutely. But by playing the long game and focusing on building relationships, you'll see the benefits in the long run. So give it a try - send one, two, or even three of these ideas to your prospects and see what happens next!

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